Diana Ross, Jennifer Hudson Surprise Fans in Chicago!

(July 11, 2019). When it comes to seeing the legendary Diana Ross in concert, you can count on three constants: she’ll open with “I’m Coming Out,” she’ll wrap up with “Reach Out and Touch (Somebody’s Hand),” usually during the closing encore, and there’ll be lots of glitz and glamour in between…whether it’s in the form of Ms. Ross’ ageless beauty, her trademark big hair or her many costume changes that mesmerize the audience with each splashy reveal.

The always larger-than-life Diana Ross on July 10, 2019, at the Chicago Theatre.

Let’s face it, with Diana Ross you come for the whole package, which includes the many years of chart-topping hits but also includes the dazzling, unapologetically over-the-top outfits: the famous body-hugging jumpsuits, the flamenco-inspired gowns with long truffled trains, the strapless dresses that come heavily accessorized with feathered shawls and cascading ruffles, the silk, the chiffon, and, of course, the oh-so-many brilliant colors.

And Ms. Ross never fails to deliver on the promise of great music and awe-inspiring splendor.

But when she performed to a sold-out crowd at the Chicago Theatre on Wednesday, July 10, the living legend had a few surprises up her feathered sleeves, and most of them happened as the show was supposedly ending.

Ms. Ross is touring the country as part of her Diamond Jubilee celebration, which kicked off with a pre-75th birthday commemoration at this year’s Grammys and has continued since with what is being officially billed as the Brand New Day 2019 tour.

The first surprise at the Chicago stop was her opening act, none other than first daughter Rhonda Ross. Rhonda was introduced as a singer/songwriter (who knew?) who was there to promote her new CD. The younger Ross launched into a 20-minute, six-song set that included her own songs plus takes on classics by Leonard Bernstein and Stephen Sondheim (“Somewhere” from West Side Story), Jill Scott (“A Long Walk”) and Adele (“Rolling In The Deep”).

Rhonda even boldly stepped into her famous mom’s territory with a rendition of the blues classic made famous by Billie Holiday, “Ain’t Nobody’s Business If I Do.”

Though not many people know this, Rhonda, 47, is a show business veteran having starred in a soap opera (she was nominated for a Daytime Emmy in the ‘90s for her role as Toni Burrell in Another World) and movies.

But musically, she’s a late bloomer with only one studio album (released in 2016) to her credit. As far as her singing went on this night, what she lacked in tonality she made up for in stage presence. She clearly enjoyed engaging the crowd (including hyping her website and an upcoming album). The crowd, in turn, warmly received her.

But this crowd was amped for mom Diana, whose first appearance – mere minutes after Rhonda exited the stage – was to “I’m Coming Out,” the Chic-produced 1980 hit that had the crowd immediately on its feet dancing and singing along. That segued into the tune “More Today Than Yesterday,” a cover of the Spiral Staircase song from the 1960s that Ms. Ross has included in her show for years now, practically making it her own during live performances.

Then came the Supremes hits, first “Stop! In The Name Of Love,” followed by “Come See About Me,” “You Can’t Hurry Love” and later “Love Child.” Those were just four of that legendary Motown group’s twelve No. 1 hits and – as the only Supremes songs of the night – Ms. Ross clearly left a bunch of classics on the table. Still, the crowd wasn’t complaining as they stood at their seats clapping and singing along to hits they’ve known and loved for more than half a century.

“Love Child” was given the special treatment by Ms. Ross’ backing band, which transformed the classic Motown tune into a lengthy, calypso-styled jam that gave Ross time for the first of five costume changes.

Upon her return to the stage, the legend delved into her disco-era hits. First, there was the Ashford & Simpson-penned 1979 tune that became her nickname, “The Boss,” followed by another Chic-produced hit, the 1980 No. 1 smash “Upside Down.”

Diana sings “Upside Down” on July 10 at the Chicago Theatre.

In its original, Chic-polished glory, “Upside Down” was Diana at her funkiest and, as many of my closest friends know, it’s my favorite song. Done live, however, the disco-era hit loses its luster as it foregoes the vision intended by Chic maestros Nile Rodgers and the late Bernard Edwards.

Still, the enthused crowd stood up for Diana’s performance of it on this night, and by the time she finished it, “Upside Down” had morphed into a ten-minute marathon that included Ross engaging the audience and inviting several fans on stage to dance and sing with her. A rousing standing ovation followed for what was ultimately one of the show’s highlights.

More disco followed with another No. 1 “Love Hangover,” followed by the latter-day Diana tune “Take Me Higher” and her main contribution to 1978’s movie musical The Wiz, “Ease On Down The Road.”

After a second costume change, Diana emerged in a striking purple and black truffled ensemble for a more mellow set that included her take on the Burt Bacharach classic, “The Look Of Love” and two Billie Holiday tunes from Ross’ Oscar-nominated acting role in Lady Sings the Blues, “Don’t Explain” and the more playful “My Man.”

Then it was back to three more No. 1 pop hits with “Theme From ‘Mahogany’,” her signature tune “Ain’t No Mountain High Enough,” and a cover of Gloria Gaynor’s “I Will Survive,” which included a snippet of the guitar solo in Michael Jackson’s “Billie Jean.”

By the time that portion of the set finished she had gone through her third, fourth and fifth costume changes, the last two of which included a sleek, body-hugging black dress that showed off Diana’s once-again trimmed down frame, and finally a flowing blue number that got the loudest applause of the night as far as her outfits went.

But it was Diana’s next move that was the most impressive.

After modeling – or more accurately showing off – the blue wardrobe wonder, Ms. Ross engaged the crowd in a sit-down chat, inviting fans to come up to the microphone – hers – and ask her anything they wanted to know. After stating nothing was off limits, she answered mostly tame questions about her next album (she’s recording it at the end of the year), her favorite song (“Ain’t No Mountain High Enough”) and who she’d like to record a duet with that she hadn’t yet.

She answered that last question by stating the singer was a guest in the audience, the Oscar- and Grammy-winning singer Jennifer Hudson of Dreamgirls fame, which generated loud applause as audience members began feverishly looking around to try and spot the singer.

When Hudson didn’t emerge right away, Diana continued answering questions like what advice she’d give to young aspiring singers to keep their voice strong for 75 years. Answer: she had no particular advice but offered that she steamed her vocal chords before shows and that each person should just stay true to themselves. Her most interesting commentary was about how she doesn’t sweat her performances anymore by fretting over whether she’ll hit all the right notes or be on key or make mistakes. It was an introspection from a lady who clearly has reached a more zen-like state in her later years.

After the eight-minute “interview,” Ms. Ross went into the traditional finish with her favorite audience participation tune, “Reach Out and Touch (Somebody’s Hand),” as the audience swayed side-to-side with hands either raised or interlocked.

Then, just as the show was ending with the band’s outro – a reprise of “I Will Survive” – up comes none other than Chicago’ own Jennifer Hudson who got a little playful scorning from Ms. Ross as to her whereabouts when she was supposed to show up on stage earlier. Diana got in quite a few digs, including chiding Hudson about not being at her 75th birthday party, noting that “Beyoncé was there.”

But the capper was when Diana asked Hudson to join her in a duet of “Endless Love,” the biggest hit of the Motown legend’s career (and her last big hit for Motown in 1981).

Diana Ross and Jennifer Hudson perform “Endless Love” on July 10, 2019 at the Chicago Theatre during Diana’s Diamond Jubilee.

Hudson obliged and performed her parts perfectly while the doting Ms. Ross led the way, singing Lionel Richie’s parts as Hudson sang Diana’s.

It was three unexpected minutes of pure heaven for fans of either artist, but especially those of Ms. Ross, who had given us far more than expected on this perfect night.

In all, there were more than 90 minutes and 22 songs worth of fun and entertainment by a looser Diana Ross, a legend who knows she’s one but wasn’t giving us that vibe during the show. She was playful, engaging, and willing to share the spotlight with others.

She was just beautiful in all her 75-year-old glory.

Diana Ross will forever be known for her exquisite showmanship, and for one more night in Chicagoland, more than 3500 people got to see why.